Thiophenol → HCID 67900867, compound

HRID 1534627Notes

Reaction equation

HRID 1534627 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=CC=1.Cl[CH:9]([C:15]([CH3:17])=[CH2:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11].O1CCCC1.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[S:7]1[CH:1]=[CH:6][CH:5]=[C:4]1[C:9](=[C:15]([CH3:17])[CH3:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

7

Reactant 4

HCID 7969ThiophenolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 14565731HCID 14565731, compound

Product 1

HCID 67900867HCID 67900867, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

A mixture of thiophenol (0.7 g, 6.36 millimole), ethyl 2-chloro-3-methyl-3-butenoate (1.05 g, 6.5 millimole), tetrahydrofuran (2 ml), and tetrabutyl ammonium bromide (50 mg) was stirred at room temperature while one equivalent (1.5 ml) of 4N NaOH was added rapidly. Stirring of the resulting two-phase system was continued for two hours (at room temperature). The reaction mixture was diluted with 50 ml of water and extracted twice with 20 ml proportions of ether. Evaporation of the ether left 1.4 g of a crude yellow oil. Flash column chromatography on silica gel gave the desired product, ethyl 2-thiophenyl-3-methyl-2-butenoate in 66% overall yield. The identity of the product was confirmed by proton NMR, carbon 13 NMR, and mass spectrum analysis.

Workup

  1. additionwas added rapidly
  2. custom(at room temperature)
  3. extractionextracted twice with 20 ml proportions of ether
  4. customEvaporation of the ether
  5. waitleft 1.4 g of a crude yellow oil

Sources & evidence

ORD record
ord-63058a0d81b449219ee2883f1510581f
Source dataset
uspto-grants-1992_02
Patent number
US05089611

Reaction notes

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